Cowboys slow-paying Dak Prescott extension coming back to haunt them in huge way

Once again, the Dallas Cowboys have decided to wait on signing quarterback Dak Prescott to a long-term deal in the offseason ahead of the final year of his contract. And once again, it's looking like the Cowboys have made a grave mistake, especially as the offseason market takes shape around them.

On Thursday, the Miami Dolphins reached an agreement with Jaylen Waddle worth $84.8 million over three years, with $76 million guaranteed. That puts Waddle at No. 4 among the league's highest-paid wide receivers in terms of annual value, which is already resetting the market at how much wide receivers are worth.

This contract, in addition to the other league-leading wide receiver contracts this offseason, will have a ripple effect beyond the wide receiver market. The payout could make a quarterback like Prescott reconsider his own contract value and prompt players across the league to renegotiate for better terms. Or, it could prompt the Cowboys to choose once again between paying Prescott and their top offensive weapon.

Jaylen Waddle deal adds pressure to Dak Prescott talks with Cowboys

Understandably, Waddle's deal could prompt Cowboys wide receiver CeeDee Lamb to push for a massive contract following his five-year rookie contract, which is slated to finish by the end of the 2024 season.

Prescott also finishes his contract in 2024 earning $34 million this year, yet the Cowboys are practically stuck between re-signing Prescott and moving on from him with a cheaper option at quarterback.

Prescott has a no-tag and no-trade clause, yet the Cowboys are saddled with a $55.5 million cap hit and only have $1.9 million in available cap space. It's too expensive to cut Prescott, but it's going to be costly to keep him beyond 2024.

Re-signing Prescott has already been a top offseason conversation for the Cowboys, with the 31-year-old quarterback clarifying last week that he "doesn't play for money" and wants to remain in Dallas. In early May, Prescott affirmed that "communication has been back and forth" as he engages in contract talks with the team. While Prescott wants to make it work with Dallas, he's also not afraid to move on and play for another team with the capacity to pay him what he's worth.

The worst part is that all of this could have been avoided if the Cowboys offered Prescott a suitable deal for his first extension in a timely manner, according to CBS' Joel Corry. If the Cowboys were proactive and re-signed Prescott in 2019 instead of 2021, they could have signed him for a deal comparable to market value at that time and potentially saved $10 million per year in his first contract extension.

Then, the Cowboys could have re-signed Prescott to a second extension worth $50 million a year in 2023. Instead, Dallas waited a year and the quarterback market has risen, with Corry predicting that Prescott could be the NFL's first $60 million player in terms of annual value. Corry expects there to be at least $150 million fully guaranteed at signing and at least $230 million in total guarantees to push a Prescott deal with Dallas over the finish line.

The Cowboys famously waited two years to extend Prescott, first by picking up his fifth-year option on his rookie deal in 2019 and then by franchise-tagging him for $31.4 million in 2020. Worse, the Cowboys signed running back Ezekiel Elliott to a six-year, $90 million deal in 2019. Elliott played four more seasons with Dallas before being traded to the New England Patriots and returning to the Cowboys on a one-year, $2 million deal.

The Cowboys should have prioritized Prescott instead then, and now with the Waddle contract, they'll be tasked with keeping Prescott and Lamb happy. Dallas may have managed before, but there may not be a path forward for Prescott and the Cowboys this time.